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EFFECTS OF ACTIVE HYDROGEN IN DIFFERENT REACTION SITES ON OXIDATION OF POLYUNSATURATED LIPIDS

Research Project

Project/Area Number 09660225
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Fisheries chemistry
Research InstitutionTokyo University of Fisheries

Principal Investigator

OHSHIMA Toshiaki  Tokyo University of Fisheries, Dept. of Fisheries, Associate Professor, 水産学部, 助教授 (70134856)

Co-Investigator(Kenkyū-buntansha) 大島 敏明  東京水産大学, 水産学部, 助教授 (70134856)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 1999: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1998: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1997: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsphosphtidylcholine / oxidation / hydroperoxide / positional isomer / cholesterol / tocopherol / arachidonic acid / liposomes / ハイドロパ-オキサイド / コレストロ-ル / トコフェロ-ル / リポソ-ム / 不飽和脂質 / 均質溶液 / リン脂質 / ラジカル開始剤 / 高度不飽和脂肪酸 / 自動酸化 / 反応場 / ミセル / ラジカル
Research Abstract

The oxidation of 1-Hexadecanoyl-2-[cis, cis, cis, cis-5,8,11,14-eicosatetraenoyl]-sn-glycero-3-phosphocholine (PC16:0-20:4) was initiated by AAPH or AMVN in a homogeneous solution of methanol or in liposomes with existence of cholesterol or alpha-tocopherol to investigate the effect of changing the environments of reaction site. The hydroperoxide positional isomers generated from oxidized arachidonyl group of the PC were converted to TMS derivatives after reduction of hydroperoxy group as well as hydrogenation of double bonds. The TMS derivatives thus obtained were analysed by mass spectrometry.
The ratio of two hydroperoxide isomers, 5-hydroperoxy arachidonic acid (5-OOH) and 15-hydroperoxy arachidonic acid, was around 1 in the oxidation of the PC in methanol. The original ratio, 5-OOH/15-OOH, obtained in the oxidation in liposomes increased to around two by addition of alpha-tocopherol with a molar ration to PC being 0.02. In more small concentration of alpha-tocopherol in the liposomes, there was no effect on the formation of hydroperoxide isomers.
These results suggested that alpha-tocopherol which coexists with PC in a liposomes bi-layer functioned as a hydrogen donor to PC and reduce the imbalance of certain hydroperoxide isomers which occurs in the liposomes system.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] T. OHSHIMA, H. USHIO AND C. KOIZUMI: "Analysis of polyunsaturated fatty acid isomerize hydroperoxides by HPLC with a port-column fluorescent detection"ACS Symposium Series 674. 674. 198-210 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X-WANG, T. OHSHIMA, H. USHIO & C. KOIZUMI: "Distribution of stereochemical isomeric hydroperoxides generated by radical oxidation of linoleic methyl ester"Lipids. 34. 675-679 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Ohshima, H. Ushio and C. Koizumi: "Analysis of polyunsaturated fatty acid isomeric hydroperoxides by HPLC with a post-column fluorescent detection. In "Flavor and Lipid Chemistry in Seafood""(Ed. by F. Shahidi) ACS Symposium Series 674, Am. Chem. Society, Washington, D.C.. 198-217 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] X. -H. Wang, T. Ohshima, H. Ushio and C. Koizumi: "Distribution of sterochemical isomeric hydroperoxides generated by radical oxidation of linoleic acid methyl ester in homogeneous solution and in aqueous emulsion"Lipids. 34(7). 675-679 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.OHSHIMA, H.USHIO, and C.KOIZUMI: "Analysis of polyunsaturated fatty acid isomeric hydroperoxides by HPLC with a part -column fluorescent detection"ACS Symposium Series 674. 674. 198-217 (1997)

    • Related Report
      1999 Annual Research Report
  • [Publications] X.H-Wang, T.OHSHIMA, H.USHIO & C.KOIZUMI: "Distribution of stereochemical isomeric hydroperoxides generated by radical oxidation of linoleic methyl ester"Lipide. 34. 675-679 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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